Will comes to live with his aunt and uncle in Bel-Air. Philip isn't too impressed by Will's behavior, especially teaching Ashley to rap and ruining his image with the members of the law firm. Vivian tries to remain neutral in all this. Carlton and Hilary look at Will with disdain.
Will starts getting used to his new lifestyle and persuades Ashley to spice up her life and stop playing the violin. He takes her to a pawn shop and she gets a new set of drums instead. Shocked by this, Philip insists on Ashley keeping up her lessons. Vivian is for it until Ashley want to give up ballet.
Will wants to go out with a beautiful girl he meets at the country club, but first he must figure out how to impress her extremely snobbish and very protective father. In order to do this, he seeks advice from cousin Carlton on becoming preppie. He must then rely on his street smarts to gain her attention.
Will tries to smooth things over between Philip and Philip's very rural parents when they visit to see Philip receive an award. The family finds out many things they did now know about Uncle Phil. When an interview goes awry, Will steps in and Philip wants to step out when his secret is told.
Will gets a visit from an old pal named Ice Tray (another guy from the streets) who, to Vivian and Philip's dismay, warms up to Hilary. Hilary also takes an interest in Tray. Will she head off in the direction Tray is headed?
Will and Carlton voluntarily drive Mr. Firth's car to Palm Springs. They get lost and drive slow to find the street. They get pulled over and arrested because they meet the description of local car thieves for whom the local law enforcement officers had been searching. Will and Carlton state a confession on live TV in an attempt to be released from jail.
Will joins the poetry club to impress a girl because he's not fitting in with this girl as he would like. What will he do the unthinkable to pull off the ruse?
The family goes to the mall to get costumes for Hilary's Halloween party. Will and Carlton compete to find a date for the party. Philip gets caught up at the gadget shop. Hilary and Ashley are detained for possible theft. Will and Vivian are discovered as singing talent.
When Will and Carlton compete for dates for a Halloween party, Will boasts of knowing famous people and Carlton weaves his tall tales. Who will win the girl? Will she be worth winning? Will and Carlton will find out.
Will surprises Geoffrey on his birthday with a gorgeous blind date whom Will promptly falls for only to be upstaged by Geoffrey. Does Geoffrey act as old as he is during his date? Does Will get the girl?
Carlton feels overshadowed by Will, who's become a basketball star at school. The competition between the two continues throughout the entire episode, but the last shot of the game will determine who is king. Is Will's conscience going to allow him to do the right thing?
Will's mom visits for the Thanksgiving weekend. When she sees that the children don't do any of the work she tells all the children to make dinner this year which turns into a disaster. Can any of the children do anything for themselves? Are they able to fix dinner? What excuses do they use to defend themselves?
Will overhears Hilary tell Vivian that she was going to go study at the library with her friend, Kimmy. After Vivian leaves the room, Hilary tells her friend she lied about going to the library and mentions she had dropped out of UCLA and lied to get away with going out elsewhere. When Will hears this, he plans to play a trick. Carlton finds out and he has a plan of his own.
Will tells Ashley's slumber-party guests a scary tale about his first day at Bel-Air Academy. He uses a little bit of truth but embellishes quite a bit to frighten the girls. Will the girls fall for his story? Will they be scared or will they see through his story?
Will decorates the mansion for the holidays, but it's garish and the neighbors are dismayed, including heavyweight boxing champion Evander Holyfield. The neighbors want band together to try and convince the Banks' to remove the decorations. Will they win their argument or will the Banks' holiday decor stay?
Philip may lose a superstitious client whom he advises not to make decisions based on Will's spontaneous remarks. Does Philip rely on a horoscope to make his decisions for the day?
Will proposes a black history class be instituted at Bel-Air Academy and gets a surprise when his Aunt Viv arrives to teach it. Will learns quite a lesson from Aunt Viv and also learns one from Uncle Phil. Will thinks he knows it all, but watch to see what all he doesn't know.
When Philip's elderly mother comes for a visit, they have different ideas on how she should recover from a cold. Philip wants mom to act her age and recover quietly while Granny has a different idea. Who wins in this battle against wills?
Will has girl problems after a date with Jazz's domineering sister who's ready to pick out a china pattern before the night is over. Even though Will thinks she's 'fine' he tries to pass her off to Carlton.
Will is on his best behavior for visiting royalty. The seemingly demure Lady Penelope has a wilder, hidden agenda in mind, though. A night on the town is more to her liking then a night at the opera. Can Will keep tabs on this wild one?
Kayla Samuels is a scholarship student whose introduction to Will opens up a different world of fun and games and romance to divert her from her studies. Does she give into Will's ways or keep up with her studies?
With Vivian gone for the weekend and Hilary in charge, it's a sure bet Will is going to get himself into trouble. When Will finds himself in debt to a pool hustler, he turns to Uncle Phil for help.
Will challenges Carlton to spend time in a tough part of town. Will doesn't think that Carlton will do it. When Carlton sells himself as a financial consultant, the gang begins to like him. Is Will got to be able to stop him?
R&B singer Tevin Campbell plays teen idol Little T, who surprises Ashley on her birthday with a special song and an invitation for a date. Are Little T's intentions good? Will Ashley be able to convince Philip to let her go on a date?
Marissa Redman is Hilary's new actress boss who wants Will as her boy toy or Hilary's glamorous job is over.